title: Application of fluorine NMR for structure identification of steroids.
abstract: Fluorinated steroids were examined using 1D and 2D homo- and heteronuclear (19)F NMR, such as (19)F-(1) H and (19)F-(13)C. The utilization of fluorine NMR accounted for spectral simplification and resulted in a straightforward pathway for the determination of structures including the configuration of these compounds; these steroids present an illustrative example for other types of fluorinated compounds, which are increasingly encountered in drug discovery. The potential of (19)F NMR is elaborated on in detail for two compounds containing diastereotopic fluorines with different coupling patterns. The analysis of the coupling patterns and the through-space interactions resulted in the determination of the structure and configuration. Heteronuclear correlation experiments, i.e. (19)F-(1)H HETCOR, (19)F-(13)C HMQC and HMBC, and (19)F-(1)H HOESY, were applied to determine first the relative stereochemistry and then the molecular configuration at C4 and C5 of a steroidal compound bearing a fused three-membered ring with two fluorine substituents. These examples proved (19)F NMR to be a useful addition to the extensively used (1)H and (13)C NMR within structure elucidation and configuration determination of small molecules.
authors.affiliation: Institute of Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
authors.forename: Kirsten A M
authors.initials: KA
authors.lastname: Ampt
authors.forename: Ruud L E G
authors.initials: RL
authors.lastname: Aspers
authors.forename: Martin
authors.initials: M
authors.lastname: Jaeger
authors.forename: Pepijn E T J
authors.initials: PE
authors.lastname: Geutjes
authors.forename: Maarten
authors.initials: M
authors.lastname: Honing
authors.forename: Sybren S
authors.initials: SS
authors.lastname: Wijmenga
mesh_terms: D002247:Carbon Isotopes / Q000032:analysis; D005461:Fluorine / Q000032:analysis* / Q000737:chemistry / Q000378:metabolism; D007553:Isotope Labeling; D008958:Models, Molecular; D008968:Molecular Conformation; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods*; D011522:Protons; D013237:Stereoisomerism; D013256:Steroids / Q000032:analysis* / Q000737:chemistry
chemical_list: D002247:Carbon Isotopes; D011522:Protons; D013256:Steroids; D005461:Fluorine